Diethyl Ether → HCID 11668986, compound

HRID 2376998Notes

Reaction equation

HRID 2376998 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]2[N:27](COCC[Si](C)(C)C)[CH:28]=[CH:29][N:30]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1.FC(F)(F)C(O)=O.CCOCC>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:12]=[CH:13][C:14]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]2[NH:30][CH:29]=[CH:28][N:27]=2)(=[O:19])=[O:18])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 21099411HCID 21099411, compound

Product 1

HCID 11668986HCID 11668986, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[2-({4-[(E)-2-(2,4-difluorophenyl)vinyl]phenyl}sulfonyl)phenyl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazole (Step 2, 110 mg) in CH2Cl2 (5 mL) was treated with trifluoroacetic acid (5 mL) and the solution stirred for 16 h, then concentrated in vacuo and partitioned between saturated aqueous NaHCO3 (20 mL) and EtOAc (20 mL). The phases were separated and the organic phase dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica (eluant 75% EtOAc/isohexane) to afford a colourless oil, which solidified on treatment with Et2O. The solid was washed with 50% EtOAc/isohexane and dried, to afford the title compound as a white solid (47 mg). δH (500 MHz, d6 DMSO): 12.11 (1H, s), 8.25 (1H, t, J 4.6), 7.85 (1H, q, J 8.1), 7.77-7.71 (2H, m), 7.69 (2H, d, J 8.4), 7.58 (2H, d, J 8.4), 7.51 (1H, t, J 4.4), 7.39-7.29 (3H, m), 7.23 (1H, s), 7.15 (1H, td, J 2.5, 8.5), 6.94 (1H, s); m/z (ES+) 422 [MH+].

Workup

  1. concentrationconcentrated in vacuo
  2. custompartitioned between saturated aqueous NaHCO3 (20 mL) and EtOAc (20 mL)
  3. customThe phases were separated
  4. dry with materialthe organic phase dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica (eluant 75% EtOAc/isohexane)
  8. customto afford a colourless oil, which
  9. washThe solid was washed with 50% EtOAc/isohexane
  10. customdried

Sources & evidence

ORD record
ord-f7234c46e9a44f2486b85797c6f2b364
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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